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Holiday Rentals in Chestertown

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Holiday Rentals in Chestertown

Amazing Modern house with a full kitchen and parking

9.8 out of 10, Exceptional, (8)
"The house is a beautiful place to stay. The location was ideal for going to attractions and stores. "
The price is €231
includes taxes & fees
13 Jul - 14 Jul
Amazing Modern house with a full kitchen and parking

HGTV quality, private guest suite, country getaway with hot tub & fire pit

10.0 out of 10, Exceptional, (5)
"Was looking for an upscale beautiful place to stay for a family wedding. Found it! Tammy has tended to every detail at this VRBO. Gorgeous farmhouse chic. Very attentive to our texts. And always good to return to Centreville to see friends and family. "
The price is €389
includes taxes & fees
1 Jul - 2 Jul
HGTV quality, private guest suite, country getaway with hot tub & fire pit

5-bedroom vacation home 5 minutes from historic Charlestown

9.8 out of 10, Exceptional, (138)
"Can’t wait to come back during warmer weather. It was a perfect over night stay. "
The price is €534
includes taxes & fees
1 Jul - 2 Jul
5-bedroom vacation home 5 minutes from historic Charlestown

Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

9.6 out of 10, Exceptional, (9)
"Great overnight stay for a wedding nearby. Would highly recommend!"
The price is €372
includes taxes & fees
1 Jul - 2 Jul
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

Bayside Cottage steps from Rock Hall Harbor

10.0 out of 10, Exceptional, (2)
"Property was nicely refurbished and furnished and well equipped. The younger set especially enjoyed the 5 bikes in good condition and the large yard to play sports. All in all, a great weekend stay!"
The price is €388
includes taxes & fees
21 Jul - 22 Jul
Bayside Cottage steps from Rock Hall Harbor

BAYSIDE BUNGALOW

10.0 out of 10, Exceptional, (39)
"Beautiful, cozy cottage. So peaceful and pretty. Owners are on site and are great people. We have stayed here several times and look forward to coming back soon."
The price is €266
includes taxes & fees
1 Jul - 2 Jul
BAYSIDE BUNGALOW

Room for an Island getaway

2.0 star property
9.0 out of 10, Wonderful, (2)
"Was a nice place for the night we were there. It had everything we needed for the night"
The price is €186
includes taxes & fees
8 Jul - 9 Jul
Room for an Island getaway

❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️

9.6 out of 10, Exceptional, (28)
"Great place and location. Not far from good food and local hot spots. Would definitely rebook and stay here again. "
The price is €260
includes taxes & fees
2 Jul - 3 Jul
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️

Luxury Waterfront Home Built for Entertaining!

2.0 out of 10, (1)
The price is €793
includes taxes & fees
1 Jul - 2 Jul
Luxury Waterfront Home Built for Entertaining!

Relax on Kent Island in 3 Bedroom Home w/Waterview

9.8 out of 10, Exceptional, (37)
"Owner was very welcoming and left a bottle of wine as a nice gesture. Excellent communication."
The price is €309
includes taxes & fees
6 Jul - 7 Jul
Relax on Kent Island in 3 Bedroom Home w/Waterview

Waterview Home by Kentmorr Marina, Beach Bar & Grill. Close to wedding venues.

10.0 out of 10, Exceptional, (38)
"Easy check-in and access to the property. Clean and stocked with everything we needed. Great rental for families!"
The price is €1,203
includes taxes & fees
14 Jul - 15 Jul
Waterview Home by Kentmorr Marina, Beach Bar & Grill. Close to wedding venues.

Waterview with Beach Volleyball! Walk to Marina & Kentmorr Beach Bar and Grill.

10.0 out of 10, Exceptional, (75)
"Property and Host were exceptional."
The price is €1,183
includes taxes & fees
14 Jul - 15 Jul
Waterview with Beach Volleyball! Walk to Marina & Kentmorr Beach Bar and Grill.

Modern and Cozy Home in Bel Air with a Home Office and Fireplace

Modern and Cozy Home in Bel Air with a Home Office and Fireplace

Hobbit House one of a kind home

10.0 out of 10, Exceptional, (5)
"Our family had a fantastic weekend here. The house fit our needs and was very relaxing and enjoyable."
Hobbit House one of a kind home

Small House on Gentleman’s Farm

10.0 out of 10, Exceptional, (11)
"Great little getaway, very clean, and the bedding was so comfy! "
The price is €264
includes taxes & fees
13 Jul - 14 Jul
Small House on Gentleman’s Farm

Oasis by the Bay - Waterfront Heated Pool Hot Tub!

10.0 out of 10, Exceptional, (1)
"The house is beautiful and on the water. Pool was great. Place was clean. Good communication from hosts. Lovely walking around the neighborhood. Short walk to views of the Bay and mouth of the Severn River. "
The price is €1,149
includes taxes & fees
9 Jul - 10 Jul
Oasis by the Bay - Waterfront Heated Pool Hot Tub!

Neptune by the Water

9.8 out of 10, Exceptional, (9)
"The house had everything we needed for a comfortable stay. We would definitely recommend this place."
The price is €562
includes taxes & fees
8 Jul - 9 Jul
Neptune by the Water

Charming Historic Row House in The Heart of Eastport's Horn Point

2.5 star property
10.0 out of 10, Exceptional, (1)
"Gorgeous little house in the heart of Eastport, walking distance to fabulous restaurants and a short hop over the bridge to dwtn Annapolis. The house was clean, well stocked, comfy beds, and the patio was a lovely little oasis to kick back in with a glass of wine at the end of the day. The host was very responsive and accommodating. Highly recommend! "
The price is €535
includes taxes & fees
21 Jul - 22 Jul
Charming Historic Row House in The Heart of Eastport's Horn Point

USNA Luxury Home, parking, pet friendly

10.0 out of 10, Exceptional, (7)
"Beautiful house in a great location to Main Street Annapolis. "
The price is €1,134
includes taxes & fees
30 Jul - 31 Jul
USNA Luxury Home, parking, pet friendly

Freshly renovated 3-story home 1 block from USNA!

9.8 out of 10, Exceptional, (34)
"It was a great place to stay- location, layout and everything else was perfect. Would stay again for sure! "
The price is €635
includes taxes & fees
9 Jul - 10 Jul
Freshly renovated 3-story home 1 block from USNA!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Frequently asked questions

Are there holiday rentals in Chestertown?

Yes, there are holiday rentals in Chestertown close to Crumpton Auction, or you can select a more secluded option if you're looking for a relaxing stay. Chestertown is known for its sporting events and university setting. Make sure you have time to check out the festivals and art during your trip.

What are some of the best holiday rentals that Chestertown has to offer?

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably: This holiday home rental outside of Chestertown offers a balcony, a garden and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 6 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

How many holiday rentals are there in Chestertown?

Expedia has 24 holiday rentals for your stay in Chestertown.

What can I see and do in Chestertown?

Enjoy the outdoors at Chestertown Dog Park and Urieville Park, or simply take in cultural attractions like Historical Society of Kent County Maryland and Garfield Center for the Arts at the Prince Theater. Rolphs Wharf Marina and Chestertown Historic District are other places to visit while you're in town.

What are holiday rentals like in Chestertown?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Chestertown. Holiday rentals offer extras like laundry facilities and kitchens to help you enjoy your stay. If you're concerned about cleanliness, holiday rentals can offer a sense of security away from shared hotel lifts and busy concierge desks while still allowing you to travel. You'll also have more space in a holiday rental than in a standard hotel, which makes a holiday rental a great option for a small group gathering.